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Cummington was first settled in 1762 and was officially incorporated in 1779. It was named after Colonel John Cummings, the original landholder.[1]

The first Congregational Church minister was Rev. James Briggs (1743 - 1825) of Norton, Massachusetts, and a graduate of Yale College around 1775.[2] Briggs was the son of Deacon James and Damaris (White) Briggs, and the husband of Anna Wiswall.

Although a small town, several Revolutionary War patriots are buried there, including Nathaniel Holbrook, Seth Wilder, Sr., and Seth Wilder, Jr.

Noted poet and newspaper editor William Cullen Bryant was born in Cummington, and returned for many years to summer in the town. His house is now preserved and open to the public as the William Cullen Bryant Homestead. The town hosts the Cummington Fair every August on the town's fairgrounds. The fair features many events including adult and 4-H exhibition halls, a craft barn, vaudeville stage, antique car parade, oxen pull, and an assortment of fair rides, games, and food stands.

The town was the subject of a 1945 documentary film, The Cummington Story, about the welcome given to a group of European refugees.[3]

As of the census[16] of 2000, there were 978 people, 382 households, and 239 families residing in the town. The population density was 42.4 people per square mile (16.4/km²). There were 452 housing units at an average density of 19.6 per square mile (7.6/km²). The racial makeup of the town was 96.42% White, 0.61% African American, 0.41% Native American, 0.31% Asian, 0.51% from other races, and 1.74% from two or more races. Hispanic or Latino of any race were 3.27% of the population.

There were 382 households out of which 24.3% had children under the age of 18 living with them, 54.2% were married couples living together, 5.8% had a female householder with no husband present, and 37.4% were non-families. 28.0% of all households were made up of individuals and 10.2% had someone living alone who was 65 years of age or older. The average household size was 2.26 and the average family size was 2.77.

In the town the population was spread out with 27.9% under the age of 18, 5.7% from 18 to 24, 30.3% from 25 to 44, 24.8% from 45 to 64, and 11.2% who were 65 years of age or older. The median age was 38 years. For every 100 females there were 102.5 males. For every 100 females age 18 and over, there were 92.1 males.

The median income for a household in the town was $42,250, and the median income for a family was $48,750. Males had a median income of $31,765 versus $27,279 for females. The per capita income for the town was $21,553. About 4.2% of families and 6.6% of the population were below the poverty line, including 5.7% of those under age 18 and none of those age 65 or over.

^"1950 Census of Population". 1: Number of Inhabitants. Bureau of the Census. 1952. Section 6, Pages 21-10 and 21-11, Massachusetts Table 6. Population of Counties by Minor Civil Divisions: 1930 to 1950. Retrieved July 12, 2011.

^"1920 Census of Population". Bureau of the Census. Number of Inhabitants, by Counties and Minor Civil Divisions. Pages 21-5 through 21-7. Massachusetts Table 2. Population of Counties by Minor Civil Divisions: 1920, 1910, and 1920. Retrieved July 12, 2011.

^"1890 Census of the Population". Department of the Interior, Census Office. Pages 179 through 182. Massachusetts Table 5. Population of States and Territories by Minor Civil Divisions: 1880 and 1890. Retrieved July 12, 2011.